


Foundations

by kittenofdoomage



Category: Supernatural
Genre: Comfort, Dates, F/M, Fluff, Multichapter, NSFW, Reader Insert, Romance, Series, Sex, Smut, Virgin Reader, explicit - Freeform, plus sized reader
Language: English
Status: Completed
Published: 2016-02-03
Updated: 2016-02-03
Packaged: 2018-05-18 02:17:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 11,314
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5894257
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: <blockquote class="userstuff">
              <p>Summary: The reader is plus sized and has never been intimate with a guy. Dean sets out to show her exactly how she's perfect in every way.</p>
            </blockquote>





	1. Chapter 1

The couch in the library looked like just as good a place as any to collapse, and your face hit the cushions with a groan. Sam chuckled at your arms and legs being flung out at all angles, before he picked up your duffel bag and put it on the table.

‘You know, you’re always having a go at us for not clearing up, then you come in and just…spread.’

'Spreadin’ is what I’m good at.’ You retorted, muffled by the cushion under your face. You didn’t even care what you looked like right now. Dean pushed your legs over, demanding room on the seat and you scowled at him before dragging yourself over to make room for him.

'So, that was horrible, I think we’re all in agreement,’ he started, referring to the messy werewolf hunt the three of you had just returned from. 'And I think that calls for beers. Possibly something stronger.’

'Oh, no, dude, I’m just gonna…’ Sam motioned towards his bedroom. 'Hit the hay. I’ve had enough for one….lifetime, actually.’ He yawned, making a little show of it as you and Dean watched him with sceptical expressions. 'Catch you in the morning?’

'Sure thing.’ Dean nodded.

'Night, Sam.’ You said, slouching into the sofa. You were totally rocking a wedgie, but you didn’t rightly care at the moment. When Sam had left, Dean lolled his head towards you.

'How about you? Gonna wuss out on me as well?’

'Hell no.’ You said, pushing at his shoulder. 'I can drink you under the…couch. Just you watch.’

Dean chuckled, before grabbing two glasses, a bottle of Jack and some beers from the small fridge they kept in the library. As he did that, you toed off your boots, listening to the elder Winchester move around behind you.

'Music?’ He asked and you nodded. Grabbing the remote to the stereo, he turned on the sound system and the low melodies of Led Zeppelin floated through the room. You smiled, then yawned, covering your mouth with your hand as you shifted on the couch. Eventually, you might retrieve your underwear from where you’d eaten it.

Dean handed you a beer and a glass, before retaking his seat. He poured himself a generous helping of whiskey, and then handed the bottle to you.

'Cheers.’ He tipped his beer towards you, and then drained it in about five seconds. You grinned, and did the exact same, leaning back again, glass of whiskey in hand. 'Tough hunt.’

'Yeah. Not the funnest.’ You sighed, staring at the glass. 'I’m surprised you didn’t head out for some relaxation time.’ You raised an eyebrow in his direction, and he picked up on what you were implying almost immediately.

'You mean, you’re surprised I didn’t go out and sleep with half of Kansas to relieve a little stress?’ He scoffed. 'Please, Y/N. You know I…’ He paused. 'I don’t do that any more. Not since…’

'Your demon Dean phase, yeah I know.’ You smiled sympathetically. 'It wasn’t you, you know.’

'I was a dick. Even more so than usual.’

You grimaced, taking a sip of your whiskey. It burnt the back of your throat, and you moaned, savouring the taste. Warm circled through your chest, settling in your belly. You were aware of Dean watching you out of the corner of his eye and you wondered if he was thinking what you were. Mostly, you were trying to avoid exactly how much of a dick Dean had been when he was a demon, specifically to you. After hunting with Winchesters for two years on and off, finding out Dean was demon had been a shock to the system.

And his black eyed self had been more than slightly nasty to you.

'I didn’t mean it, you know.’ He said quietly, not looking at you anymore, his hands cradling his glass.

'I know. Wasn’t you.’ You repeated, trying to ignore the hurt mixing with the whiskey in your mouth, leaving a sour taste. Washing it down with more Jack was the only option. You filled up your glass again.

'And it wasn’t true either.’ His voice was still quiet and laced with guilt.

'I know.’ You didn’t really want to talk about it, but apparently Dean needed to alleviate some guilt.

'And I -’

'Dean, please.’ You could feel a lump forming in your throat and you threw back the glass of whiskey in one gulp, trying to ignore the sting of tears. _How long you been in love with me, huh, Y/N? You really think I’d look twice at you, back then or now? I mean, you can’t go past Wendy’s without eating a pint of ice cream. I don’t know how a Wendigo hasn’t plucked you for winter storage yet. You’d last long enough._ It hadn’t been him. The nasty, hurtful things he’d said were designed to do just that, to hurt you.

'I’m sorry.’ He kept his eyes on the table in front of the couch, drinking his whiskey gingerly. 'I just…I never…I never apologised. For any of it.’ He looked at you then. 'And I never meant to mock your feelings.’

'What feelings?’ You scoffed, feeling the effects of too much whiskey, too quickly. 'There are no feelings. Everyone knows that Sam is the hot one.’

'Now I know you’re lying.’ Dean chuckled, glad you were easing the tension. He wasn’t even sure why he’d brought it up. 'I’m clearly the better looking brother.’

You shook your head, putting your empty glass on the table. 'I drank that…too fast.’ Wiggling in your seat, you scowled, standing up, no longer caring. With a quick rearrange, you sat down again, relieved at last.

'What was that about?’ Dean looked at you in concern.

'Wedgie.’

'Oh.’

You gave him a pointed look. 'You know how many times I’ve caught you rearranging the crown jewels, Dean Winchester? You and Sam both. Always think I’m not looking.’

'Why are you looking?’ He said, and you blushed bright red.

'I-I, I’m, I mean,’ he was chuckled now and you picked up the cushion you’d faceplanted earlier, throwing it at him. 'You’re such a douche at times.’

'Only at time?’ He finished his drink. 'Huh. Need to work on that.’

'Shut up.’

The two of you fell into companionable silence, as you poured yourself another whiskey, not caring for the effects any more. You needed to relax and getting drunk was just how to do that. Dean took the bottle when you were done, giving himself a generous helping. Long moment passed as you sat on the sofa, your eyes shut.

'Never have I ever…’ Dean started and you laughed.

'Seriously?’

'Yeah. Come on. I’m bored and there’s not exactly any board games around here. Plus, we don’t get to spend much time together. And Sam is a party pooper.’

'Sam is plenty of fun.’ You defended the absent Winchester.

Dean made a funny noise. 'Never have I ever had a crush.’ You scowled at him and took a drink, watching as he didn’t.

'You’ve never had a crush?’

'I don’t do crushes, sweetheart. If I want something, I go for it.’

'Even when you were a little kid? There wasn’t like, a celebrity or something…’ He shook his head and you blinked in surprise. 'Never saw that coming.’

'Your turn.’

Your eyes rolled of their own accord. 'Okay, fine. Never have I ever…flown in a plane.’

Dean took a drink, grinning. 'Never have I ever worn a dress.’

You giggled. 'That’s too easy. You’re trying to get me drunk.’

'You’re already drunk.’ He pointed out and you shrugged. 'Your turn again.’

'Never have I ever…driven Baby.’

'Boring.’ He said, but drank anyway. 'Never have I ever….had sex in a tree.’ He looked at you as you didn’t drink, and shrugged. 'Well, I guess that’s something. I can’t imagine it being comfortable.’

'Never have I ever…’ You paused for a moment and then thought of one. 'Never have I ever shoplifted.’

'Oh please.’ Dean wiggled his fingers before taking a drink. 'Fastest fingers in the west, darlin’.’ His awful cowboy accent made you giggly loudly. 'Never have I ever been on a rollercoaster.’

'Really?’ You took a sip. 'You’re missing out.’

'I’ve got enough horror in my real life without fake thrills, Y/N.’ He said, seriously. 'Your turn again.’ You could feel the effects of the whiskey now, hear the slight slur in your voice and you leant back against the couch back, flinging an arm over your face.

'Never have I ever…’ You paused. 'Had sex.’

Your words were met with silence and you lifted your arm, peeking out at Dean. He was stared at you in shock, confusion written all over his face.

'Aren’t you gonna drink?’ You asked quietly, and he lifted his glass, but didn’t drink just yet.

'You’ve…never?’ He asked, lowering the glass again and you sat up, feeling slightly judged. Shaking your head, you stood from the couch, picking up the empty beer bottles. 'Y/N, wait -’

'No, it’s stupid, I shouldn’t have said anything, really.’ You plastered a fake smile on your face, but it waned quickly. 'It was a joke. Just forget it.’ His warm fingers encircled your wrist, pulling to back to face him. Tears shone in your eyes and you suddenly realised exactly how drunk you were.

'Y/N…what the hell? I can’t believe…I guess I just assumed…’

'Yeah, well, assuming and you make an ass out of me.’ You muttered, trying to pull your wrist free. 'I just…never had occasion, okay? I mean, look at me. I’m huge in comparison to other girls. I’ve got a spare tyre that makes me look like the Michelin Man’s lovechild, arms and legs like tree trunks and my ass has got more badunkadunk than an entire issue of Busty Asian Beauties.’ You shook yourself loose from him. 'No man would look at me naked and not run for the hills.’

'Be a fucking idiot if he did.’ Dean snapped, and you took a step backwards, taking his words the wrong way.

'I’m not looking for a pity fuck, Dean. Especially not from you.’

'What do you mean, especially not from me?’ He stood up, realising how upset and drunk you were. 'Is this because of -’

'God, just drop it!’ You practically shouted. 'I get it, okay? I’m fat. Why do you think I hunt? Because it’s all I’m good for. I tried dieting and all that crap, but it doesn’t work. I’m always gonna be a “big girl”,’ your tone was laced with self-hatred. 'At least being a hunter, I can do some good, because it’s about all I’m ever gonna do!’

'Y/N…’

'Forget it.’ You wiped furiously at your eyes, refusing to look at him. 'I’m going to bed.’

'Y/N…’ He reached for you again, and you scooted out of his reach, tripping over your own drunk feet and falling, your head colliding with the corner of the library table. You cried out, tears spilling of their own accord, and Dean was at your side in a instant.

'Great, now I can be a fat girl with a black eye.’ You sobbed loudly. 'I’m a fucking mess.’

'You had too much to drink.’ He muttered, checking your face. You were right – your right eye was already swelling and you were gonna have a nice shiner in the morning.

'Just let me go to bed. I’ll sleep it off and we can forget that…this ever happened.’ You finished miserably, rejecting his help as you got to your feet. Leaving the library behind you, you fled to your room.

You never saw the dejected expression on Dean’s face turn into a look of resolve.

*****

Waking up the next morning, you immediately groaned and hated yourself. A quick trudge to the bathroom indicated that you had indeed drunk too much – your hair was a mess, you’d fallen asleep in your clothes, and the damage to your right eye was to the point that you could barely see out of it.

Running a brush through your hair quickly, you located some clean clothes that didn’t smell like they’d been washed in hops, and left your room, hoping to locate a bag of frozen peas to cover your face and bring the swelling down.

Emerging into the kitchen, Sam instantly saw the injury and frowned. 'What the hell happened to you?’

'Whiskey.’ You replied, practically grunting at him. 'I fell.’

'You…fell?’ Sam’s head reared back in surprise. 'That’s…oh, hey, someone left these for you at the bunker door. I didn’t think we got post. Mind you, the delivery guy was as freaked out as I was.’ You grabbed a bag of peas from the freezer, then looked at what Sam had on the table.

A dozen brightly coloured flowers, wrapped in paper, sat on the kitchen table, a card with them.

'I didn’t read it.’ He said, munching on his cereal. 'I didn’t know you were seeing someone.’

'I…’ You wandered over, peas in your hand, mostly forgotten. 'I’m not.’ Your voice was a whisper, and you picked up the card, reading the inscription. It had an address for a restaurant in town, and indicated a reservation for Friday at eight. Today was Wednesday. 'I can’t go to this. I’ve got a battered face and nothing to wear.’ You turned the card over. 'Besides, it doesn’t say who it’s from.’ You offered the card to Sam, who took it and inspected it. 'Nope. Printed, so can’t even trace the handwriting. I can look into it on the computer if you’d like.’ He handed you the card as you considered his proposal, and then he grinned.

'They’re nice flowers though.’ He commented. 'Wild flowers and orchids. Orchids represent strength, whilst wildflowers are more commonly used to represent thoughtfulness.’ His smile faded a little. 'Come to think of it…these are Dean’s favourites.’

You baulked. ’D-Dean’s?’

'Yeah.’ Sam ran his fingers over the bouquet. 'Our mom…she used to grow orchids, and she’d always keep wild flowers in the house, fresh ones at least once a week.’ His smile returned. 'Dean sent you these.’

'Sam Winchester. Master of deduction.’ Dean said from the doorway, making you jump in shock, the peas clattering to the floor. He stepped forward, picking them up. 'Apparently I can’t do anything mysterious around here with him about.’

'You sent me flowers?’ You asked. 'And…dinner?’ Your eyes flickered to Sam who was watching the exchange with mild interest, and you became suspicious. 'Why?’

Dean shrugged. 'I got you drunk last night and you hurt yourself.’ He was lying through his damn teeth. 'And I wanted to make it up to you.’

'I can’t go to dinner at a nice restaurant looking like this.’ You gestured to your face.

'Cas can fix it.’

'That’s not…Dean…’

'Sam, could you excuse us for a moment?’ Dean asked his brother, who nodded, picking up the flowers.

'I’m gonna go put these in water. It’d be nice to have some flowers around here.’ He walked off with the bouquet, and you whirled on Dean.

'I said I wasn’t interested in a pity fuck, Dean.’

'This is _not_ that.’ He glared at you. 'This is…look…it occurred to me, last night, that you’ve never been shown exactly what a _real_ man is like. I mean, if you think someone is gonna judge you based on your size -’

'I don’t _think_ , I _know_.’ You retorted, feeling tears in your eyes again. 'Stop trying to make me feel better. I know damn well you aren’t attracted to me.’

Dean frowned. 'And why do you think you know that?’

'Look at me!’ You laughed, and it was bitter sound. 'I’m about three times the size of any girl you’d look at. I live in jeans and baggy shirts. I’m completely not your type.’ You shook your head. 'Don’t do this, Dean. Because it’ll only end up hurting more.’ You dropped the card to the table and moved passed him, only stopping when he grabbed your arm.

'You’re so stupid.’ He said, and you scowled.

'Just an F-Y-I, _that_ isn’t how you get a girl to go out with you.’

'No.’ He stuttered. 'I mean, that…geez, you don’t make this easy.’ He sighed. 'Please, Y/N. Just one date. If you still think I’m faking then we’ll drop it. But I’ve known you a few years now. I don’t want you to think because men have been a dick to you in the past…because I’ve been a dick…that you aren’t worth something. This isn’t a game to me.’ His voice was softer than you’d ever heard it and you stared at him, feeling your resolve melting away. 'Please.’ He was practically begging.

'One date?’ He nodded, and you sagged in his grip. 'Fine. One date.’ He smiled, and you pulled out of his hold, escaping back to your bedroom.

One date wasn’t going to change anything. There was no way Dean Winchester was feeling anything but pity for you.


	2. Chapter 2

By Wednesday evening, Castiel had turned up at the bunker, and he’d happily fixed your eye, warning that you’d best stay away from table corners in future. You’d laughed with him, the presence of your angel friend putting you at ease. Castiel was easy to talk to – despite what others said about him – because he never usually had another agenda. Maybe in another life you’d have liked him, but he was too good a friend.

Funny how you didn’t think that way about Dean. Sam was the same as Cas; you could appreciate the aesthetic attractiveness about both men, but the thought of so much as kissing them made you feel slightly green. Dean was…Dean was a nightmare.

And he was making it worse with this whole stupid date idea. Of course it wouldn’t go further than the first date. For one, you hunted together and lived together. For another, he _knew_ you weren’t his type and he _knew_ about your crush you’d harboured for years – how could he not?

This was just a sympathy ploy. “Let’s make the fat girl feel better about herself”. You scowled at your reflection in the mirror, before glaring at your wardrobe. What did he even expect you to wear? Jeans and a baggy shirt? You knew the place he was taking you to and it was high end. You’d never fit in. You’d spend the whole night with people looking at you like a freak, thinking there must be something wrong with Dean for him to be seen out in public with someone like you. You’d order and salad and sit there feeling like the fattest person in the world.

‘Y/N?’ Sam’s voice interrupted you from your self-hatred. He smiled as he pushed your bedroom door open a little. 'Everything okay?’

'Aside from your brother being a complete mental case?’ You sighed, moving over to your bed and falling onto the mattress. 'This whole thing is stupid. I have no idea what he thinks it will achieve.’

Sam smiled tightly, sitting next to you on the bed. 'Dean’s very fond of you, Y/N.’

'We’re friends, Sam. And honestly, we both know I’m not his type.’

The younger Winchester shook his head. 'I don’t think Dean has a specific type. If he wants it…chances are he’ll get it.’

You looked at your best friend speculatively. 'I don’t even have anything to wear. You know the restaurant right?’ He nodded. 'I literally own three pairs of jeans, and about a dozen shirts. I don’t think I even have a nice bra I can wear. And you can forget matching underwear.’

He grinned. 'Well, that’s why I came to see you.’ Pulling a credit card from his pocket, he waggled his eyebrows at you. 'Mall’s still open for another couple of hours. Gotta love those Christmas opening times. How’s about a nice little shopping spree, courtesy of Mr James Davidson?’

You smiled, shaking your head in disbelief. 'We don’t normally use cards for that, Sam.’

'No. But this is special. And you deserve it.’ He grabbed your hand. 'Come on. You can help me pick out some new shirts too. Most of mine have too many blood stains now.’

'And that would be the weird life we lead.’ You giggled, grabbing your coat as Sam pulled you towards the door.

Retail therapy was definitely helpful.

*****

Friday morning rolled around with a snowstorm, and you climbed out of bed somewhat reluctantly. The bunker was useful for a lot of reasons, but being half underground, it could get damn cold. You located your thick fluffy socks by the foot of the bed and pulled them on before braving actually putting your feet on the stone floor. One of the things you’d have to sort out was getting some rugs in this place.

Sneaking through the bunker, checking the time, you found Sam already up. He smiled at you through the mop of messy bed hair he usually displayed, and pointed to the coffee maker.

'You want some?’

'Yes please.’ You yawned widely. 'Dean up yet?’

'Yeah. But I think he went back to his room.’

'Okay.’ You took a seat in the kitchen, shivering. You’d spent the last day or so buried in books, trying to distract yourself from tonight’s activities. 'Sam, I’m still not sure about this.’

'Oh, come on.’ He said, placing a cup of coffee in front of you. 'We talked about this. At length. Dean wouldn’t do this out of sympathy.’ He grinned. 'We both know he’s too much of a dick for that.’

'He’s not a dick.’ You said, looking into your drink as if it held the answers to the universe. 'But this is a mistake. He’s not gonna…he’s not…ugh. I can’t even hate myself properly.’

Sam’s grin dissolved into a frown and he reached over to take your hand. 'Y/N, you’re one of very few people I love, and I gotta be honest, seeing you beat yourself up like this makes me kinda wanna punch you.’ You blinked, Sam’s method of comfort coming across as mean. 'You see yourself as this…this whole other person. We don’t see that. We see our friend. And, I can’t speak for Dean, but maybe you should let him have this chance to prove he sees more than that. Don’t write him off.’

His words sank in and you nodded slowly. 'Fine. I’ll give him a chance.’

'You did spend all that money on a whole killer outfit.’

'I wouldn’t call it killer.’ You giggled. 'But it’s probably the nicest thing I’ve ever owned.’

'And you said you felt comfortable in it.’

'Yeah, in a changing room. Maybe in my bedroom. Out in public?’ You shuddered. 'Scary place.’

'Used to blending in.’ He said, understanding. He wasn’t a stranger to public anxiety, although it was for different reasons. 'Look, just chill out today. Have a bath, pamper yourself – you bought all that stuff to do it. Maybe if you get bored, we’ll call Cas and see if he’ll let us pluck his eyebrows.’ He was making jokes to make you feel better now, but you didn’t mind. You had a feeling if Cas thought it was conductive to your well-being, he probably _would_ let you pluck his eyebrows.

'Good idea.’ You grinned, finishing your coffee, wincing a little at the heat flowing down your throat. 'I’m gonna go get a couple more hours. Besides, it’s warmer in my bed than it is out here.’

'Yeah. I might see if we can get hold of some space heaters. Even I’m feeling the cold.’ He remained in the kitchen as you padded back to your room, almost on tip-toes the whole way. As you passed Dean’s room, you noticed he had his door open slightly, and he was busy on the other side of his bed, humming as he worked on whatever he had down there. Pausing for a moment, you listening, hearing rustling, and recognising the tune he was humming as Metallica’s “For Whom The Bell Tolls”. You smiled, before creeping onward to your room.

*****

Friday evening came too quickly, and you’d spent most of the day pampering yourself, which was something you hadn’t been able to do in a _long_ time. Allowing yourself the opportunity to dress up in nice clothes, and put on make up, despite your misgivings, was actually nice, and you found yourself glad Dean had suggested this, no matter what the outcome was.

Leaving your room, you stepped down the hall in the simple black ballet pumps you’d picked to go with your black dress trousers and the sparkly red top that accentuated your cleavage and still hung loose around the ribs, so you felt comfortable. You’d wanted a black cardigan to go with it, but Sam had insisted on the red one to match.

'Red is Dean’s favourite colour on a woman.’ He’d winked, and you’d rolled your eyes, but gone with his suggestion.

Coupling the outfit with some nice jewellery (and it had been _forever_ since you’d bothered to put earrings in), and a clutch bag containing your phone, and of course, your gun because you never knew what was going to happen, you felt a little more confident. You’d put your hair in a simple style, away from your face, and you’d kept your make up light but sultry.

Sam was sitting in the library when you poked your head around the corner. He was alone, and you frowned, stepping out fully. His eyes lit up when he saw you and he smiled.

'You look fantastic.’ The compliment made you blush.

'Where’s Dean?’ You asked.

'He’s picking you up at half seven.’

Your frown turned to confusion. 'Picking…me…up? But…he lives here.’

Sam chuckled. 'He wanted to do things properly.’

'He’s sitting outside in the car, isn’t he?’ You rolled your eyes, turning towards the door.

'Y/N. We talked about this. Let him do what he’s planned.’ You stiffened, hearing a knock at the bunker door. It was loud and make your blood turn to ice in your veins. You couldn’t do this. Stepping back, you were met with the solid wall of Sam’s chest, and he turned you, bending his knees to look you level in the eye. 'Don’t run. Don’t back out. If nothing comes of it, it’s because he loves you as a friend. But don’t pass up an opportunity for happiness, Y/N.’ His eyes sparkled, as if he knew something you didn’t, but you didn’t press, simply nodding at him. 'I’ll get the door.’ He squeezed your shoulders before releasing you and heading for the door.

'Hi, here to pick up Y/N?’

'You’re a goof.’ Sam’s voice deadpanned, and you heard the sound of a fist hitting flesh. A few seconds later, Sam came down the steps grinning, and rubbing his chest. 'I’ve warned him that you have to be home by midnight.’

'Sammy…’ Dean’s voice warned from the top of the steps and you couldn’t help but giggle, the tension in your body broken. You made your way up to the door, and Sam smiled at you.

'Be safe, kids.’

'I’m gonna hit him again.’ Dean said, and you smiled as you rounded the corner to see him stood at the door, looking jaw-droppingly gorgeous.

He’d shaved, but only enough to tidy up the week old scruff along his jaw, and his hair was smoothed back, freshly cut at the sides. He wore a slick black suit with a deep red shirt that seemed to make his eyes even more of a vivid green. It wasn’t like the fed-suit you’d seen him in before, and somehow you had the feeling he’d been out on a little shopping trip too. He’d left the shirt open a couple of buttons at the top, giving a nice view of the hollow of his throat, his Adam’s apple bobbing above it as he swept his eyes over you.

'You look…’ You didn’t realise you were holding your breath. 'Absolutely gorgeous.’ He finished, blushing a little, although you weren’t sure why. You should be the one who was embarrassed to be seen in public with this specimen that was _clearly_ out of your league.

And just like that, the butterflies came rushing back.

'Thanks. You look pretty nice too.’

'Oh this? Nothing. Really.’ He smiled, offering his arm. 'Shall we?’ You nodded, slipping your arm through his and pulling the bunker door shut behind you.

The ride to the restaurant was short, and neither of you spoke along the way. You weren’t sure was to say, and Dean was busy humming again. You knew he did that when he was either busy or nervous, and you didn’t see what he had to be nervous about. For all intents and purposes, he was wining and dining a troll.

Pulling into the parking lot, he rushed out of the car to come round and open your door, and your cheeks reddened as he did so, taking his hand, even though it wasn’t really necessary. You’d climbed out of this car with a knife wound in your belly before now. But it was nice, nothing you’d really experienced before, as he locked the car and led you to the venue for the night’s meal.

'Table for two under Winchester.’ Dean kept his voice clear as he spoke to the maître d, and the thin looking member of staff peered down his nose at you, prompting you to shrink back, and Dean to scowl. 'Problem?’

'Of course not, sir. Right this way.’ He picked up two menus, leading you and Dean to a table, and you felt like every single person in the place was staring at you, wondering why you were on the arm of such a guy. You could take down ghosts, werewolves, wendigos and an army of demons besides, but right now, this restaurant was the most terrifying thing in the world.

The table the man had led you to was in the centre of the restaurant, and you took your seat, picking up the menu as Dean asked for the wine list. Maybe if you hid behind it, no one would see you.

'Hey, Y/N.’ Dean said quietly. 'The menu won’t suck you in.’ He chuckled. 'That guy was a douche. Checking out your boobs like some kind of perv.’

'He wasn’t checking me out, Dean.’ You said, lowering the menu. 'He was judging me.’

Dean scowled. 'Well then he’s even more of a douche.’ The douche employee returned, handing Dean the wine list with a condescending sniff.

'Would you like me to run through it for you, sir?’

The hunter opposite you bristled, and then smiled, giving it a dangerous edge. 'No, it’s cool, Bosworth. I got it.’ The maître d turned away, his attitude stinking up the place as he walked. 'I can’t kill him can I?’

Dean’s blunt dislike of the man broke the ice and you giggled. 'No, Dean. We’re supposed to be having a nice evening. That normally doesn’t include homicide.’

'Darn it.’ He grinned, and you smiled back. 'Well, I’m gonna pick us a nice wine. Despite my uncouth attitude, I do know a good wine when I see one.’ A waiter came over, seemingly a nicer member of staff, and took the order for the wine, returning a few moments later with the crisp bottle straight out of the fridge. Dean watched as he poured two glasses, thanking him.

'So, what are we eating?’ He asked, browsing the menu. 'I like the sound of that sirloin steak.’

'It’s really expensive in here.’ You said, frowning at the price of a simple salad.

'Don’t you be looking at that salad section.’ He warned. 'You eat what the fuck you like, Y/N. Not like we’re paying for it. And you don’t have to put on a show for me.’ He leaned forward. 'There’s no one who can best me at a cheeseburger eating competition like you.’ You blushed at his lewd smile, which seemed to satisfy. 'Nothing wrong with enjoying your food.’

'No. There isn’t.’ You said, feeling a little more at ease. Your eyes went back to the menu, and you smiled. 'Ooo, lasagne, my favourite.’

'Done.’ He grinned. 'I’m not bothering with a starter. It’s all too posh sounding anyway. Best not be that gourmet crap, or we’ll have to find a diner for pancakes afterwards.’ You giggled, knowing Dean could probably eat a horse in a single sitting. It was one of the things you liked about him, his voracious appetite for food, as well as life. Despite being a hunter, he enjoyed the simple things.

The food was ordered, and you settled into easy conversation with your “date”. You spoke about high school, your favourite subject, and what you’d wanted to be before you’d fallen into your current “job”. Dean revealed he’d always dreamt of being an astronaut, but obviously he’d known that would never happen. As the conversation flowed and dinner arrived, the wine joined it, but you didn’t feel drunk. Mostly, you felt warm, comfortable and amazed that it was Dean sitting opposite you making you feel like this.

'I guess I never had the smarts.’ He finished explaining something and you frowned.

'You’re plenty smart, Dean.’ You admonished.

'Not as smart as Sam.’ He grimaced, picking at the vegetables that had come with his steak. 'Never could be.’

'Maybe not, but there’s not many people as smart as Sam.’ You pointed out. 'You’re not stupid, Dean, you shouldn’t believe that.’

'And yet, when I tell you the same thing when you say you’re fat and ugly, you don’t listen to me.’

You blushed. 'Point taken.’ You pushed your plate a little further away. 'I am so full. Definitely not gourmet.’ He grinned.

'It was good food. And that snotty nosed waiter seems to have left.’ He raised his hand for the check. 'Do you wanna get out of here?’

'Where to?’

He wiggled his eyebrows. 'That’s a surprise.’


	3. Chapter 3

Settling into the passenger seat of the Impala, you relaxed a little more as Dean started the engine. It was steadily getting colder outside, and you shivered, pulling your coat around you as Dean turned the heaters on.

‘This weather is getting a little frosty.’ He joked, pulling the Impala out onto the main road, which had been cleared quickly by the snow ploughs, leaving large drifts at either side of the road. 'At least we’re warm from the nice dinner and wine.’

'It was.’ You smiled over at him, surprised as he reached over and squeezed your knee gently with his large hand. A blush covered your cheeks, and you looked away. 'Good food and good company. It’s all you need really.’

Dean chuckled. 'A good view helps too.’ He said, pulling off of the main road rather quickly, the old car trundling down a side road. The snow hadn’t been cleared as much here, and had been compacted down into a thin layer of ice by the traffic, and Dean kept going slowly, leaning forward slightly over the wheel. 'Ah, here we are.’ He pulled into a lay by at the side, near a thick expanse of fields. There were no houses in sight, and nothing else visible.

You frowned, looking around. 'And here is?’

'I wanted to show you something.’ He climbed out of the car, going round to the trunk and rummaging through. He pulled out a thick blanket and shut the trunk heavily, before opening your door. You climbed out, a little hesitant, your ballet pumps not providing much protection against the icy ground.

'I really don’t understand.’ You said, wobbling a little, Dean’s strong arms coming around you to steady your balance.

'You will.’ He threw the blanket around your shoulders and stepped behind you, nudging the door of the car shut with his hip. 'Just shut your eyes.’

You did as asked, but the frown remained on your face, even as Dean’s hands settled firmly on your hips, guiding you forward. The blanket provided an extra layer of warmth against the cold air, your breath appearing almost instantly in a cloud before you. Dean’s breath was hot on your neck and you shivered a little, more from his closeness than anything.

'Sorry it’s so cold.’ He assumed that was the reason for your shivers. 'But, with Christmas coming, it’s kinda nice that it’s actually wintery. Makes this easier.’

'Oookay.’ You said, as his fingers tightened on your body, you slowed, stopping entirely as he held you still. 'Dean…what are you up to?’

'You can open your eyes now.’ He whispered, keeping close to you. You opened your eyes, a little shocked at first by the brightness of the scene in front of you.

The fields were covered by a thick blanket of snow, the air so still that nothing moved or made a sound. All you could hear was your own heart beating, and Dean’s soft breathing behind you, a small cloud of his breath moving in front of you every moment. The moon was bright and full, causing a sparkling effect on the white snow, providing such a contrast that it took your breath away looking at it, and you gasped lightly.

'Wow.’

'See,’ he started talking, his mouth close to your left ear. 'A lot of people moan about the snow. It’s cold, it’s wet, it’s dangerous…’ He smiled against your neck, placing a soft kiss to the skin there. 'But a lot of people miss it’s beauty.’

'What are you getting at?’ You asked quietly.

'You keep saying you’re all these negative things. And you keep assuming that I’m one of _those_ people; but you’re so wrong. I’ve seen how beautiful you are from the moment I saw you. All fire and spunk, determined to prove everyone wrong and fighting so hard that you constantly out do me and Sammy. You’re the best of us, Y/N. Yet you seem to think you’re the worst.’

Tears pricked at your eyes and you glanced down, away from the bright field in front of you. Dean moved, keeping one hand on your waist as he walked around in front of you, his spare hand lifting your chin up so you met his bright green eyes. They were wet too, and he gave you a lopsided grin.

'You thought this whole date thing was about making you feel better about yourself, and you’ve assumed that I could never be interested in you.’ You opened your mouth to protest, but were immediately silence by Dean’s thumb running over your bottom lip. 'Don’t argue. I know it’s what you’re best at.’ His grin became a soft smile. 'But you need to realise – there’s a lot more to you than your looks, Y/N. And even if there wasn’t – you’re the most beautiful girl I’ve ever seen. Inside and out.’

Your mouth was still open, but you were unsure of what to say, too stunned by his words to even manage a coherent thought. Dean’s chin dipped, and his face moved closer to yours and all at once, your body went still with fear and excitement as he closed his eyes.

He was going to kiss you.

And you’d wake up, because this was obviously a dream.

But as his soft, warm lips pressed against yours and your eyes closed in response to the caress, you realised that this dream had come true and you weren’t going to wake up. Almost instinctively, your foot twitched, ready to raise off the ground in some kind of clichéd Disney move – this was the first, _real_ , emotion-filled kiss you’d ever experienced. Everything before now became a faded memory, hazy and clouded in comparison to this single moment where Dean Winchester, the man you’d crushed on for so long, was kissing you in the snow.

All too soon, it was over, and Dean’s breath was soft on your lips as he moved away. He didn’t move far, keeping you wrapped in the cocoon of his arms, his hand leaving your chin to pull you closer. You didn’t even notice the cold now, and you weren’t ashamed to admit you were more aroused by that one single kiss than you’d ever been in your entire life.

'I think I should get you back to the bunker.’ He said, smiling down at you and you nodded, sad that the evening had to end.

Sliding into the passenger seat of the Impala, you smiled as Dean started the car and took your hand, keeping his fingers threaded through yours the entire way back. You couldn’t keep the dopey grin off of your face, even as he walked you to the bunker door, unlocking it and guiding you inside. Sam was nowhere to be found, and you were surprised as Dean accompanied you to your bedroom door.

'I could ask you in for coffee.’ You said, pushing a strand of hair out of your eyes. 'But…I don’t have a coffee maker in my room.’

Dean grinned again, looking down as he held both of your hands in his significantly larger ones. 'I’m not going to come in tonight. I still think you might not be believing how I feel here. So I’m going to be a gentleman, go back to my room, and think of you all night long.’ There was a heavy undertone to your voice, and part of you wanted to drag him inside and to bed. But he was right – the other part of you didn’t believe this wasn’t a trick, didn’t believe he truly wanted you.

Maybe you were still waiting to wake up.

Dean reached into his suit pocket, pulling out a small piece of mistletoe. 'It’s Christmas in two weeks. I’m gonna take that time to prove it to you.’ He held the mistletoe up, over your head, smiling down at you. 'You know what this is for, right?’

You nodded, your eyes glancing upwards, before you raised up onto tip toes and kissed him softly.

'Goodnight, Dean.’

'Goodnight, Y/N.’ He placed the mistletoe in your hand, and stepped back, watching as you opened your door, not leaving until you were inside.

Leaning against the door, you grinned like an idiot and slid down a little way, holding the sprig of mistletoe tightly.

Dean Winchester was something else entirely. And the next two weeks were going to be amazing.

*****

The next morning, you awoke slowly, stretching languidly before the previous night came back to you. A smile spread over your face and you rolled over, picking up your phone. A text message was waiting on the screen, and as you opened it, the smile on your face widened.

_Had such a good time last night x Dean_

Propping yourself up on one elbow, you fired off a text to him in reply.

_Why are you texting me from across the hall, doofus? x Y/N_

With a yawn, you sat up, reading for your large fuzzy socks, already feeling the cold as you shrugged off the covers. Your phone bleeped again, and you picked it up, reading the message eagerly, the stupid smile apparently permanently fixed on your face.

_It’s too warm in here to get out of bed. I had this idea to go take a beautiful girl out in the snow last night and it was cold._

You blushed, walking down the hallway, seeing his bedroom door closed. With a roll of your eyes, you carried on to the kitchen, finding Sam already up, with a fresh cup of coffee.

 _Well, I’m up and in the kitchen already_.

Sam beamed at you as you took a seat at the table. 'You look happy. I assume last night went well?’

'It did.’ You said, accepting the offered cup of coffee. Your phone beeped again. 'Your brother is…surprising.’

'He has his ways.’ Sam grinned, tucking into the bowl of cereal he’d made for himself as you checked your phone again.

_Hmm. Breakfast date?_

_Do I have to change out of my pyjamas?_

_I’m not._ Dean’s reply made you laugh, and you heard his bedroom door open down the hall. Without the smile fading, you got up and poured Dean a coffee, just as he walked into the kitchen, throwing a greeting towards his brother. He came up behind you, taking the coffee, placing a soft kiss to your cheek, which made you blush like a schoolgirl.

'Well. You two are…’ Sam swallowed his mouthful. 'Cosy. It’s nice to see you both smiling.’

Dean grinned, following you back over to the table. 'Well, I need to do some shopping. Christmas and all. Thought we could make a proper holiday of it this year.’ Sam blinked at his brother’s suggestion as you eyed Dean curiously. He seemed a little offended by the reactions. 'What? I like Christmas.’

'We haven’t celebrated it in years, Dean.’

'No. But this year…’ He looked over to you, his hand finding your knee under the table and squeezing it. 'We’ve got stuff to celebrate alongside it.’ You blushed, looking down at your coffee as Sam chuckled.

'Get a room.’ He muttered, finishing his breakfast.

'There’s no rush.’ Dean retorted, but his eyes were focused on you. 'So, need to pick out decorations. Fancy a trip to the mall? I’ll buy you lunch?’

You shook your head. 'I’m buying. You paid for dinner.’

'Technically -’ He started, and you smacked his shoulder lightly, causing him to laugh. 'Okay, okay. Lunch is on you.’ He looked over at his brother, wondering if he should ask him, but the younger Winchester shook his head.

'No, you guys go ahead. I’ve got some research to do. Make sure there’s no cases about.’ He smiled, and you returned the gesture as Dean picked up his coffee and sipped at it.

'Well, that’s settled. An hour, in the garage, Y/N.’

 

**One week later**

 

Christmas was fast approaching, and Dean had stayed true to his word. Between the two of you, the bunker had a tree and decorations, and was feeling very festive. You’d indulged in a former hobby, cooking up a storm for the boys, who had appreciated the efforts. Dean, especially, had been impressed, loving everything you were doing.

He’d also impressed you, with his eagerness to woo you properly. Flowers, chocolates, walks in the snow, cuddles in front of films in the library, giving you kisses as he walked past you – everything he’d done was amazing, and he’d put no pressure on you for anything else. Except you were about ready to jump his bones.

The Friday before Christmas Day, he came up to you in the kitchen, holding out two tickets to the cinema. You frowned, taking them, and your eyes lit up when you saw what he’d done.

'Star Wars? Really?’ You bounced on the balls of your feet.

Dean smiled. 'Of course. Sammy’s going to go to the same showing but he’s sitting elsewhere. We’ve got back row seats.’ He wiggled his eyebrows and you frowned at him.

'Dean, I’m not going to go to the cinema to see the most anticipated film of the year, and make out with you during it.’ Not that you were going to complain about his making out abilities. It was as far as you’d gone so far, and Dean was very insistent on taking it slowly.

'No, but we can make out during the trailers.’ He grinned, and you slapped his forearm. 'Okay, I forgot. Trailers are one of your favourite bits.’ You handed the tickets back to him. 'Now, go and get ready. I wanna be out of here soon. Need to get popcorn and drinks, and make sure we’re comfy.’ Turning away, you shrieked as he tapped your ass with his hand, chuckling as he did so.

'Dean!’

'You love it.’

Dean was well behaved the whole way through the film, and you came out gushing, practically nerding out with. 'And when the Falcon appeared, it was amazing, and that bit with the…’ You carried on, oblivious to the stupid smile on Dean’s face as he watched you. He’d known you’d be over the moon at seeing the film, and he’d picked it for that very reason.

'Hey, where’s Sam?’ You asked suddenly, pausing in your appraisal of the new Star Wars.

'He’s…gone back to the bunker.’ Dean said.

You frowned in confusion. 'With the Impala?’

'Yeah.’

'So how are we gonna get home?’

'We’re not.’ He answered simply, taking your arm and leading you down the sidewalk. It was cleared of ice, the slush gathering in the gutter from the most recent fall. Lebanon wasn’t a big town, but it was a nice town, and the buildings were old. It made for a nice walk, if you hadn’t been so confused.

'Dean…what are you planning?’

'Well,’ he looked down at you, smiling as he pulled you close. 'We’re going to walk through town, pick up a bottle of wine, and…’

'And what?’

'I booked us a room at a four star hotel. The Lodge, I think it’s called. It’s just down this street, past the mini-mart.’ He shrugged as you stared at him open mouthed, continuing to walk beside him, almost on auto-pilot. 'We don’t have to do anything, I just…I thought a night in a nice warm hotel room with room service and just us would be….nice.’ His voice faltered, and you didn’t respond, unable to form the words. 'Unless you’d rather just go home, I can call Sam and -’

Your lips on his cut him off suddenly, and he found himself struggling to stay upright on the slippery pavement as you kissed him breathless. Your foot found a patch of ice and you stumbled, giggling as Dean caught you. 'Sorry.’ Your giggles continued. 'I just…you’re so romantic. I never would have thought it.’

'Just tell me one thing.’ He said, holding you close as he wound his arms around you, completely ignorant of everyone else on the street. 'Have you noticed anything?’ You frowned, confused by the question, and Dean smiled. 'You’ve stopped panicking. You’re not worried about what anyone else is thinking any more. We went to that diner on Sunday and you smiled the whole time. Tuesday, when we had to go speak to that family about the ghost three towns over. Did you feel like they were judging you? Or how about -’

'I get the point, Dean Winchester.’ You grumped, pulling him a little closer. 'I get it. I just…you make me happy.’ Your voice ended a little negatively and he shook his head slightly.

'You’re waiting for the other shoe to drop, aren’t you?’

'I still…’ You bit your lip, pulling back a little, despite his grip on you. 'I guess I’m still waiting for you to realise I’m not -’ He cut you off with a kiss this time, but he kept it brief.

'I don’t know what else to do to prove it to you.’ He said, pressing his forehead to yours. 'Except to take you to this hotel, and show you the only way I really know how.’ Heat bloomed in your belly, and you nodded mutely. 'I’m not leaving you, and I’m not leading you on. I’m not doing this because I pity you, Y/N.’ His green eyes bore into yours. 'I’m doing it because I’m in love with you.’

Your breath hitched in your throat, and you went red for a second, unsure of how to respond. Finally, you swallowed down your nervousness, smiling up at him.

'Where’s this hotel?’

*****

In your mind, you’d still be kissing Dean when he pulled you into the hotel room, his hands all over you, and you’d have the confidence to pull at his jacket and shirt, all the while telling him exactly what you wanted.

In reality, you were blushing like the virgin you were as he unlocked the door, before taking your hand and leading you inside. The room was big enough, and the bed looked superbly comfortable. A television was mounted on the wall opposite the bed, and as Dean placed the bottle of wine he’d brought on the table, you stood awkwardly by the door, unsure of what to do.

It wasn’t like you were a complete innocent. You’d done stuff. Never gone all the way – by the time it came to the “getting naked” portion of the evening, you’d always come up with an excuse. A guy having his hand down your pants was completely different to being exposed to them, no clothing to hide the squishier parts of you that you hated.

And despite Dean’s attempt to make you feel at ease, and the success he’d had with taking you and making you feel like a fucking queen – all those insecurities and fears came rushing back far too easily.

For his part, Dean noticed.

'You’re…nervous.’ He surmised, coming up close to you, his hands reaching out and you nodded, unwilling to meet his eyes. You knew he was smiling, and the little voice in your head told you he was probably laughing at you. 'I’m not gonna rush you, sweetheart. You know that.’ He glanced over to the bed. 'How about, you take your coat off and get comfortable on the bed, we’ll find something awfully trashy to watch on the TV and I’ll pour us some wine?’

He was at it again. Dean Winchester – master of seduction. You nodded, pulling off your jacket as he went back to the table, locating two glasses in the mini-bar. He poured the wine as you tested the mattress, finding it soft and yielding, climbing onto it as you kicked your shoes off. Dean approached the bed, offering you your glass as he placed his own on the bedside table. You sipped at the wine as he unlaced his boots and threw them off, before grabbing the remote and literally throwing himself onto the bed, causing you to shriek as you tried to contain the wine in your glass.

'Let’s find somethin’ to watch.’ He drawled, slipping an arm around you. You relaxed into his side, placing your drink on your side of the bed. After flicking through a few channels, Dean’s face lit up. 'Oh hey, _Love Actually_.’

'You _like_ this film?’ You asked, a little taken aback and Dean nodded.

'It’s funny, it’s got some brilliant actors in it, and hey, it’s a Christmassy film.’ He grinned, pulling you closer to drop a kiss on your forehead. 'What’s not to like?’

You giggled, placing one hand on his chest as you sighed into his embrace. As the film went on, you felt more and more comfortable, and when it got to the part with Hugh Grant dancing, Dean had shifted down the bed, practically laying down with you.

It didn’t come as a shock when he glanced over at you, smiling. 'I dance like that when no one is watching.’

'Really?’ You asked. 'Think you’d ever dance like that for me.’

'Baby, I’d dance for you any time.’ He chuckled, and you felt the mood shift, his face hovering close to yours before your lips met. He was soft and gentle, his fingers tilting your chin up a little, allowing him to slip his tongue into your mouth. It was different to every other time he’d kissed you.

This time felt like it wasn’t going to stop.

His body shifted against yours, and you felt his arousal hard against your thigh, stirring the arousal in your belly to new heights, and you realised you weren’t going to run away this time. You trusted Dean implicitly, and that included trusted him with your heart.

He reached around, sliding his hand over your ass, pulling you closer to grind against you and you keened against him, enjoying the feel of his fingers sliding over your body, even through the jeans you were wearing. As you started to grind back against him, he broke the kiss, his eyes glazed and pupils blown, the movie forgotten.

'You are the most amazing girl I ever met, Y/N.’ He whispered and you blushed, before feeling a rush of confidence.

'Lay back.’ You asked, pushing lightly at his shoulder and he looked at you, confused by your sudden boldness, but doing as you asked. With shaking fingers, you reached for his belt, undoing it quickly, your hands making quick work of the buckle and the button underneath, until the pressure he’d felt of his jeans against his cock lessened and you reached inside, freeing him. The noise he made as your hand encircled his length only made you bolder and you sat up, watching his eyes close in bliss.

Pushing his trousers down, you watched your hand slid up and down, the slit at the top of his cock weeping with pre-cum as Dean hissed, watching you carefully. He must have read your intention on his face as he covered your hand with his, pumping along with you.

'That feels amazing,’ He said, quietly, arching his head back.

'I know some stuff.’ You said, confidence flooding your voice for the first time. You weren’t lying. Bending down, Dean’s eyes widened as he realised your intention, and you peeled his fingers away, flicking your tongue out to taste him. His hips thrust a little, and the sexiest little growl erupted from his lips as you licked the pre-cum from his cock.

'Fuck, Y/N…’ He grunted again, his hand reaching out to stroke your back. 'Fuck…baby…’ You slid your mouth down over him, enjoying the power you had over him at that moment, the feel of his cock pushing against the roof of your mouth, the taste of his essence on your tongue. 'Fuck, Y/N, don’t stop.’ You smiled, before sucking your cheeks in and bobbing your head a few times, moving your tongue at the same time along the bottom of his cock, tracing the veins. He hissed and growled, before gasping, his hand curling into your side. 'Fuck, that’s, fuck, baby, don’t…oh shit.’ His hips jerked and you released him, sitting back.

'You got a dirty mouth, Dean Winchester.’

He scowled. 'You surprised me.’ Sitting up, his cock bouncing as he did so. 'I wasn’t expecting that.’

'I said I was a virgin. I’ve never had sex. I never said I’d never done anything.’ Your words seemed to strike something inside him and he pounced, pinning you to the bed, his cock digging into your thigh, hard and insistent.

'You are full of surprises.’ He grinned. 'I love it.’ You giggled as he kissed you again, before his hand slid down over your torso, over the body you hated so much, copying the movements you’d made on his pants only moments before. As his warm fingers glided along the top of your pubic mound, you gasped, your teeth clenching over your bottom lip. 'Now, let me surprise you.’

He was slow, purposeful, as his index finger found your clit, teasing it gently before pushing further into your wetness, probing your folds.

'You’re so wet for me, baby.’ You whimpered, closing your eyes, your hand on his bicep as he continued to explore you. 'Has anyone ever done this?’ You nodded. 'Has anyone ever eaten you out?’ Another nod. 'I never thought you’d have sucked cock before.’ You gasped, his filthy words only inspiring the orgasm you could already feel approaching. 'And you’re so fucking good at it.’ He dipped one finger into your wet passage, opening you up for him. 'So fucking wet, can’t wait to see you underneath me. Can’t wait to watch you writhe on my cock, baby.’

That was it, you came undone, clinging to him as he continued to work his fingers inside you, prolonging your orgasm. When you were finished, Dean pulled his hand from your jeans, licking his fingers clean and damn if it wasn’t the hottest fucking thing you’d ever seen. He grinned when he’d finished, gesturing to his cock.

'Even your taste gets me going.’ He thrust against you, somewhat hampered by the jeans around his thighs.

'Dean…’ You keened, pulling him close to taste him. You didn’t want to wait any more, and you pulled at his shirt, wanting to feel him. Somehow, he’d banished those fears and nerves, and you didn’t care any more, simply wanting him. And he didn’t disappoint.

Pushing his jeans and boxers down, he kicked them off of the end of the bed, before pulling his shirt off, baring himself to you, as if he knew that him getting naked first would be easier. Then he knelt up, his fingers hooking into the sides of your jeans and pulling them down, along with your panties. You closed your eyes tightly, knowing he’d see your tree trunk thighs, the cellulite on your legs, and you waited…only to find Dean crawling back up your body, his cock nudging at the aforementioned thighs, before his mouth descended on yours.

'It’s not enough.’ He whispered against your lips. 'I need to see all of you.’ You blushed, feeling the urge to run rising up in your throat, your bravado dwindling again. 'Don’t hide from me.’ He begged. 'There’s not a thing about you that I don’t love.’ He held himself up on one arm, before using the other to push your top up, distracting you with kisses as he unhooked your bra and pulled it down. He didn’t pull off your shirt right away, his fingers too busy twisting and teasing your nipple into a point before paying attention to freeing your other breast. When your top was bunched up, he stopped kissing you, bending his head to suck at one breast, then the other. 'And these are fucking gorgeous.’ He said, massaging you softly.

He helped you pull your top over your head, and you were finally naked underneath him. Your hands moved, ready to cover up the parts, the _everything_ you hated, but Dean stopped you, pinning your wrists over your head, his mouth on yours once more.

'Don’t.’ His single word command stopped you dead. 'I’m not running from you, Y/N. Please don’t run from me.’

You melted, relaxing against him, his hand releasing your wrists when he felt you wouldn’t bolt.

'Dean…’

'Y/N?’

'I didn’t…’ You swallowed, loving the feeling of his strong body pressed against yours. 'I didn’t bring…anything.’

He seemed to produce a foil packet out of nowhere, and you blushed as he knelt up, his eyes caressing your body like his hands had, and he smiled. 'You’re fucking gorgeous, Y/N.’ The blush deepened, but you still had to physically force yourself not to cover up. Dean ripped open the foil packet, rolling the condom down over his cock, before he took it in hand, rubbing the head against your entrance. You tensed, suddenly aware you were about to have sex for the first time. He noticed and frowned.

'Baby, calm down.’ He said quietly. 'Not gonna rush this.’ He bent over, kissing you again. 'Don’t wanna hurt you.’ You nodded, feeling his fingers probing at your entrance again, teasing and stroking you, before he slipped one finger inside you. Your walls gripped at him hungrily, before he added a second finger, scissoring them slowly inside you, his mouth moving from your lips to your nipple, sucking hard. His cock bounced against your thigh, and you moaned loudly against him, bucking your hips.

'Dean…please…’

'Are you sure?’ He asked, still using his fingers to fuck you. 'I don’t…’

'Dean, please!’ You repeated, grabbing at him with your hand. 'Don’t wanna wait anymore.’

He nodded, pulling his fingers from your wetness, before lining up his cock. 'I’m gonna go slow. You control this, Y/N. Don’t wanna hurt you.’ His repeated need to not cause you pain made you fall for him even more, and you reached up, pulling him close. His lips collided with yours as he pushed inside you, filling you more than you’d ever been filled before. Of course, there was no resistance in his way – you might a virgin, but it wasn’t like you’d never pleasured yourself.

Except Dean Winchester felt _way_ different to any vibrator or dildo you’d ever encountered. He was soft, but hard a steel, his flesh splitting yours apart in way you weren’t sure you’d ever experience again. As he bottomed out, his balls pressed against your ass, you groaned, closing your eyes when he stopped to let you get adjusted to his size.

'You okay?’ He asked, focusing his green eyes on your face. You nodded, opening your eyes to look at him as he started to move, slow, deliberate strokes into your pussy.

Fuck, this was going to hurt tomorrow, but somehow you didn’t care. You’d be quite happy to die right here, giving up your virginity to the fucking sex god that was Dean.

'You’re so beautiful.’ He whispered, holding you close, his hands wandering over your body, somehow finding every single spot that turned you on, one arm hooking under your knee to bring it up and giving him a new angle to drive his cock into you. 'So responsive, so fucking wet for me, Y/N.’

You wished you could reply with dirty talk but when you opened your mouth, all that came out was a moan of his name and a whimpered beg for more. He obliged, of course, slamming his hips into yours vigorously. As he shifted, his dick punched into your sweet spot, and you fell, hard and fast, clenching around him so hard that he winced and pounded into you even harder.

'Dean!’ You cried out, coming harder with every thrust.

'Jeez, I can’t…I can’t…fuck, Y/N…’ His lips sought yours out as he held you closer, his fingers pressing into your skin as he came hard into you, his cock pulsing against your sensitive flesh.

You were sweating by now, and Dean was panting against you, reluctant to pull away.

'Anyone would think I was the virgin.’ He said, laughing at himself. 'I should have been more impressive than that.’

You giggled, and he groaned at the sensation of your body vibrating around his cock, still sheathed inside you and more sensitive now he’d climaxed. 'Sorry, but if you think that wasn’t impressive…’

'I’ve done better.’ He admitted. 'But we’ve got all night.’

'Can I have some recovery time?’ You asked, flinching a little as he pulled out of you to dispose of the condom. 'I’m a little…sore.’ You admitted and he smiled, throwing the condom into the bin before locating his pants. You found yours, pulling them on as Dean chucked his shirt at you.

'That’ll be easier access.’ He said with a wink, and you smiled, pulling his shirt over your head. He was a big guy,and the shirt was a good fit. As you sat up fully, looking over at the television to see where the film was, Dean groaned. 'Seeing you in my shirt…fuck me, Y/N.’ He fell down beside you. 'We should have done this a lot sooner.’

You sighed, letting him pull you into a cuddle on the soft mattress. 'I wish.’

'Came true, didn’t it?’ He kissed the top of your head.

'Yeah.’ You smiled. 'Yeah, it did. But you did a damn good job of laying the foundations.’

Dean grinned. ‘You get it now though? That I’m not going anywhere.’ You nodded, burrowing into his side. ‘Good. Cos I love you, Y/N, and that ain’t ever gonna change.’


End file.
